MODIFICATION OF THE PICTET-SPENGLER REACTION IN THE SYNTHESIS OF FUSED 2,3-BENZODIAZOCINES

被引:2
|
作者
Tolkunov, A. S. [1 ]
Baumer, V. N. [2 ]
Palamarchuk, G. V. [2 ]
Shishkin, O. V. [2 ,3 ]
Mazepa, A. V. [4 ]
Tolkunov, S. V. [1 ]
Bogza, S. L. [1 ]
机构
[1] Natl Acad Sci Ukraine, LM Litvinenko Inst Phys Organ Chem & Coal Chem, UA-83114 Donetsk, Ukraine
[2] Natl Acad Sci Ukraine, Inst Single Crystals, Res Branch Chem Funct Mat, UA-61001 Kharkov, Ukraine
[3] Kharkov Natl Univ, UA-61077 Kharkov, Ukraine
[4] Natl Acad Sci Ukraine, AV Bogatsky Physicochem Inst, UA-65080 Odessa, Ukraine
关键词
3-amino-2-[2-(3,4-dimethoxyphenyl)ethyl]quinazolin-4(3H)-one; fused diazocines; hydrochloric acid; tetrahydroquinazolino[3,2-c][2,3]benzodiazocin-15-ones; trifluoroacetic acid; cyclization; Pictet-Spengler reaction; N-NITRENES; INTRAMOLECULAR REACTIONS; DERIVATIVES; ALKENES;
D O I
10.1007/s10593-011-0867-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the synthesis of the eight-membered heterocyclic skeleton of tetrahydroquinazolino[3,2-c][2,3]benzodiazocin-15-ones, based on the Pictet-Spengler reaction of 3-amino-2-[2-(3,4-dimethoxyphenyl)ethyl]quinazolin-4(3H)-one with carbonyl compounds in acidic media, is proposed.
引用
收藏
页码:1006 / 1013
页数:8
相关论文
共 50 条
  • [31] Pictet-Spengler reaction on solid support.
    Guo, LQ
    Yang, LH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 124 - ORGN
  • [32] Unexpected cis selectivity in the Pictet-Spengler reaction
    Bailey, Patrick D.
    Beard, Mark A.
    Phillips, Theresa R.
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3645 - 3647
  • [33] The Pictet-Spengler Reaction in Nature and in Organic Chemistry
    Stoeckigt, Joachim
    Antonchick, Andrey P.
    Wu, Fangrui
    Waldmann, Herbert
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8538 - 8564
  • [34] Peptides and peptidoaldehydes as substrates for the Pictet-Spengler reaction
    Pulka, Karolina
    Slupska, Marta
    Puszko, Anna
    Misiak, Maria
    Wilczek, Marcin
    Kozminski, Wiktor
    Misicka, Aleksandra
    JOURNAL OF PEPTIDE SCIENCE, 2013, 19 (07) : 433 - 440
  • [35] The cis-specific Pictet-Spengler reaction
    Alberch, L
    Bailey, PD
    Clingan, PD
    Mills, TJ
    Price, RA
    Pritchard, RG
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (09) : 1887 - 1890
  • [36] Total Synthesis of (+)-Yohimbine via an Enantioselective Organocatalytic Pictet-Spengler Reaction
    Herle, Bart
    Wanner, Martin J.
    van Maarseveen, Jan H.
    Hiemstra, Henk
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 8907 - 8912
  • [37] Pictet-Spengler reaction on solid support.
    Yang, LH
    Guo, LQ
    TETRAHEDRON LETTERS, 1996, 37 (29) : 5041 - 5044
  • [38] Mechanistic studies on the asymmetric Pictet-Spengler reaction
    Van Linn, Michael L.
    Cook, James M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [39] Asymmetric Synthesis of the Indolo[2,3-α]quinolizine Alkaloid (+)-Cuscutamine via a Diastereoselective Intramolecular Pictet-Spengler Reaction
    St Pierre, Max
    McNulty, James
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (41)
  • [40] Application of hexamethylenetetramine in a Pictet-Spengler type reaction for synthesis of isoquinoline derivatives
    Ivanov, I
    Venkov, A
    HETEROCYCLES, 2001, 55 (08) : 1569 - 1572